3-Chloro-4-(3-chlorophenyl)-2-butanone → [5-(3-Chloro-benzyl)-4-methyl-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

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Reaction Steps

A suspension of 78.7 mg (0.3 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea and of 71.6 mg (0.33 mmol) of 3-chloro-4-(3-chlorophenyl)-2-butanone in ethanol (3 ml) was heated over night to reflux to yield a yellow solution. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was purified on silica gel with methylene chloride/methanol 19/1 yielding 55 mg (43%) [5-(3-chloro-benzyl)-4-methyl-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a yellow solid. MS ISP (m/e): 425.1/427.2 (100/43) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.16 (s, 1H), 7.64 (s, 1H), 7.53 (s, 1H), 7.35-7.19 (m, 6H), 7.01 (s, 1H), 4.01 (s, 2H), 3.78 (s, 3H), 2.24 (s, 3H), 2.14 (s, 3H).

Provenance & Evidence